Tetrahydrofuran → HCID 59427331, compound

Participants

Reaction Steps

N5-(7-methoxy-1,5-naphthyridin-4-yl)pyrimidine-2,5-diamine (90 mg, 335 μmol), 1-chloro-4-phenylphthalazine (97 mg, 403 μmol), THF (1677 μl, 335 μmol), and LiHMDS (1006 μl, 1006 μmol) were added into a pressure tube. The mixture was stirred at RT for 10 min. A red solution was formed. The tube was placed in a preheated oil bath at 100° C. After 1 h, LCMS showed complete conversion of SM to product. The reaction was cooled to rt. Hexane was added to induce the product to precipitate out of the reaction mixture. The resulting red solid was filtered with an aid of hexane. LCMS confirmed that the solid was the product. The product was purified by performing a column chromatography on silica gel using 60:40 CH2Cl2:(90:10:1 CH2Cl2:MeOH:NH4OH). Yellow solid was obtained. LCMS confirmed product. HPLC showed 96% pure. 1H NMR showed rotamers. Note: this cmpd was slightly soluble in DMSO at rt. MS Calcd for C27H20N8O: [M]+=472. Found: [M+H]+=473.

Provenance & Evidence